‘Is It Even Worth It to Try and Date Again After Divorce?’
Dear Emily,
After ending a tumultuous 25-year marriage, I took the time recommended by my therapist of not even thinking about dating for nearly two years (one month for every year married). I learned a lot about myself — how much I love being single, living in my little apartment, and spending my time however I want, even if that means scrolling TikTok until three in the morning. My mantra for the first year was “I can do hard things,” and I did. I am just now beginning to think I might want to begin dating again. I’m not interested in ever getting remarried or really getting into anything serious, but I would like to get out and have a little fun.
But I also have some doubts. I’m using dating apps for the first time in my life and fumbling around like a newborn. My first day on Bumble, I accidentally swiped the wrong way so many times when I was just trying to navigate the screen. So far, I’ve had someone offer up how willing they were to move across the country “for the right person” within the first five minutes of our conversation, someone obviously using a translation app who just wanted my bank-account information, and several very homely men bragging about their abilities in bed. I also live in a red state, and it’s so hard to find a middle-age man who isn’t a Trump supporter. It feels like the pool of potential matches is so small. Can I even find someone who’s worth the effort?
On top of all that, I have my own insecurities of being in my 50s and contemplating dating for the first time in decades. While I look pretty good for my age, it’s a vulnerable spot to be in. How willing am I to let someone into this peaceful little world I’ve created? What happens the first time they see me without makeup? Or when I take my Spanx off and parts of me look like a busted can of biscuits? I’m finally happy with myself. I don’t want to ruin that.
How can I protect myself while wading back into the world of dating? Is it really worth it to try?
Sincerely,
Successfully Single
Dear Successfully Single,
I think it’s only worth it to keep trying app dating, and dating in general, if you feel like you can add something valuable to the already happy, self-sufficient life you’ve built. Unfortunately, that’s a question only you can answer. Being intimate with new partners does open you up to vulnerability, and it will challenge the contentment you’ve worked hard to rebuild by yourself. But if you can maintain a sense of self-worth that doesn’t depend on what men think of your body, mind, and personality, you’ll be able to date and still feel the sense of freedom and self-determination that you feel now. Easy-peasy, right?
The only problem is that we’re programmed from birth to judge ourselves according to an unrealistic beauty standard based on perpetual youthfulness, and we’ve also been conditioned to defer to men’s opinions about everything. This happens on a subconscious level, and it happens to all women, of all ages, and there’s very little we can do about it except be aware that it’s happening and consciously work to challenge it. Dating men, especially in the image-focused world of the apps, is bound to push you right up against these issues. But you’ve said that your mantra your first year post-divorce was “I can do hard things,” and this might be another hard thing you can do, if you’re willing to try, and if the opportunity for fun outweighs the potential challenge.
I asked my friend Betsy, who, like you, is divorced after a long marriage, about her experience on the apps. She’s a bit older than you, at 63, and is currently taking a break from dating, but she offered up some basic guidance. First and foremost, she avoids red flags, after learning the hard way that having “run with the bulls” in a profile is one of them, so watch out for that one. (Other red flags: “So many men on boats with fish, so many Game of Thrones chairs.”) It also helps to have a group of supportive friends to laugh with about men’s collective “assholery.” In general, she tries not to take the whole thing too seriously, even though, unlike you, she’s not in it just for fun — she’d like to eventually find a partner. She’s not looking for perfection, just someone kind and compatible. “I know some people think it’s a numbers game, but for me, it’s the opposite; it’s weeding out numbers. Because I do not want to spend another hour of my life across from a guy who doesn’t look me in the eye the entire time, or doesn’t ask me one question about myself, or … doesn’t show up at all,” she says. “I have TV shows to binge. I do think it’s worth a try, of course! But it can be a long game, so I think it can require a lot of patience.”
She also attests that if what you want is just to sleep around with 25-year-olds, that is in fact a real option (she’s serious). (She can’t bring herself to do it, though: “They look like babies to me!”)
Based on what I learned from Betsy, and what you’ve said about the life you’ve created and what you want for yourself, it might indeed be worth continuing to play with the apps, with all their moments of awkwardness and potential for flat-out failure. If you can make yourself keep trying, you might just find a connection real enough that it’ll make you forget about the self-consciousness you feel about your face without makeup or your body without Spanx; those will be the last things on your mind when you’re in the throes of real fun (by which I mean sex).
As for the MAGA of it all: The potential downsides of app dating in a red state are pretty daunting, and it would be understandable if you didn’t want to subject yourself to the pitfalls that will undoubtedly ensue if you keep swiping. Your life is so good right now, and it’s only worth introducing new men to it if they aren’t Trump-y assholes. Given all this, it might be worth trying some of the more old-fashioned means of meeting people before you dive wholeheartedly into the world of the apps. Maybe consider some IRL activities that will bring you into contact with men who share your values. Apps aren’t the only way to meet new people, even though they are undoubtedly the easiest! You could volunteer for a local cause or politician, or participate in a project like a community garden or a soup kitchen. Even if you don’t meet anyone you want to make out with directly from these activities, it could enlarge your social circle in a way that might unexpectedly lead you to someone cool.
You might find that the pool of potential matches in the real world is larger than you think. Or maybe you’ll find another way to enjoy being by yourself, just as you have been during the past two years of your journey. While dating can be fun, it’s just as important to hold on to the insight you’ve already gained: You now like your own company enough that adding another person to the mix is just a bonus, not a necessity.
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